CN106660961A - 作为抗蠕虫药的新的磺酰基氨基苯甲酰胺化合物 - Google Patents

作为抗蠕虫药的新的磺酰基氨基苯甲酰胺化合物 Download PDF

Info

Publication number
CN106660961A
CN106660961A CN201580046065.2A CN201580046065A CN106660961A CN 106660961 A CN106660961 A CN 106660961A CN 201580046065 A CN201580046065 A CN 201580046065A CN 106660961 A CN106660961 A CN 106660961A
Authority
CN
China
Prior art keywords
alkyl
unsubstituted
halogen
amino
group
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CN201580046065.2A
Other languages
English (en)
Other versions
CN106660961B (zh
Inventor
N·高维里
C·塔陶易
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Elanco Tiergesundheit AG
Original Assignee
Novartis Tiergesundheit AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Novartis Tiergesundheit AG filed Critical Novartis Tiergesundheit AG
Publication of CN106660961A publication Critical patent/CN106660961A/zh
Application granted granted Critical
Publication of CN106660961B publication Critical patent/CN106660961B/zh
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/18—Sulfonamides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/10—Anthelmintics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/56—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C307/00—Amides of sulfuric acids, i.e. compounds having singly-bound oxygen atoms of sulfate groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C307/04—Diamides of sulfuric acids
    • C07C307/10—Diamides of sulfuric acids having nitrogen atoms of the sulfamide groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/09—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton the carbon skeleton being further substituted by at least two halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/10—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of a saturated carbon skeleton containing rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/14—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/21—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
    • C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/26—Radicals substituted by halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/56—Amides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/61—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/65—One oxygen atom attached in position 3 or 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/84—Nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
    • C07D215/06—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
    • C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/30—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/34—One oxygen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/12—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D263/48—Nitrogen atoms not forming part of a nitro radical
    • C07D263/50—Benzene-sulfonamido oxazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
    • C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
    • C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/38—Nitrogen atoms
    • C07D277/44—Acylated amino or imino radicals
    • C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/54—Nitrogen and either oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
    • C07D279/12—1,4-Thiazines; Hydrogenated 1,4-thiazines not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C07D285/135—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/155—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
    • C07D295/26—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D309/06—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/66—Nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/28—Halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/025—Boronic and borinic acid compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
    • C07C2602/40—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing six carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
    • C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Quinoline Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pyridine Compounds (AREA)
  • Pyrane Compounds (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Indole Compounds (AREA)

Abstract

本发明涉及新的式(I)化合物或者其对映异构体或盐，其中变量具有权利要求中所示的含义。式(I)化合物可用于控制脊椎动物内或脊椎动物上的寄生虫，特别是体内寄生虫。

Description

作为抗蠕虫药的新的磺酰基氨基苯甲酰胺化合物
本发明涉及新的磺酰基氨基苯甲酰胺化合物，及其在控制温血动物体内寄生虫例如恶丝虫(heartworms)中的用途。
犬恶丝虫(Dirofilaria immitis)是通过蚊子叮咬从宿主向宿主传播的寄生线虫。终宿主是狗，但是其还可以感染猫和其他温血动物。尽管通常称作“恶丝虫”，成年蠕虫实际多半寄生于肺动脉系统(肺动脉)，对动物健康的主要影响是损害肺导管和组织。偶发地，成年恶丝虫迁移至重度感染的右心脏，并且甚至大静脉。恶丝虫感染可引起宿主的严重疾病。
恶丝虫感染可用基于砒霜的化合物对抗；治疗是耗时、麻烦的，并且经常只是部分成功的。因此，主要关注点是预防恶丝虫感染。目前，仅通过全年定期向狗、猫和其他温血动物施用大环内酯类例如伊维菌素、莫昔克丁或米尔倍霉素肟，实现恶丝虫预防。不幸地，在USA的一些地区，已观察到犬恶丝虫对大环内酯类即将出现的抵抗。因此，亟需发现新类型化合物，其通过预防或通过直接杀死不同阶段的恶丝虫，可有效控制恶丝虫感染。现在，已令人吃惊地发现一组新的磺酰基氨基苯甲酰胺化合物，其可有效控制温血动物的体内寄生虫，包括有效控制恶丝虫。
发明简述
因此，根据一实施方案，本发明涉及式(I)化合物或其盐或对映异构体，
其中
n是0或1；
A是C1-C6-烷基；C1-C6-卤代烷基；C3-C6-环烷基；C3-C6-卤代环烷基；含有选自B、N、O和S的1-3个相同或不同杂原子的5-或6-元杂环烷基，其是未取代的或进一步被卤素、C1-C4-烷基或C1-C4-烷氧基取代；或者是苯基，其是未取代的或被下列基团取代：卤素、C1-C6-烷基、C1-C6-卤代烷基、C3-C6-环烷基、C3-C6-卤代环烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C1-C6-烷硫基、C1-C6-卤代烷硫基、C1-C6-烷基-亚磺酰基、C1-C6-卤代烷基亚磺酰基、C1-C6-烷基磺酰基、C1-C6-卤代烷基磺酰基、SF5；氨基，N-单-或N,N-二-C1-C6-烷基氨基，三-C1-C4-烷基硅烷基，C1-C6-烷氧基羰基，氨基羰基，N-单-或N,N-二-C1-C6-烷基氨基羰基，氨基磺酰基，N-单-或N,N-二-C1-C6-烷基氨基磺酰基，C1-C6-烷氧基羰基氨基，N-C1-C4-烷基-N-C1-C6-烷氧基羰基氨基，氰基，硝基，或者未取代的或卤素-、C1-C4-烷基-、C1-C4-卤代烷基-、C1-C4-烷氧基-、C1-C4-卤代烷氧基-、氨基-、氰基-或硝基-取代的C3-C6-杂环基；或者是肉桂基(cinnamyl)，其苯基基团是未取代的或被卤素、C1-C4-烷基或C1-C4-烷氧基取代的；或者是杂芳基，其还是未取代的或者被卤素、氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C2-C4-烷酰基、5-或6-元杂环烷基-C1-C2-烷基或者未取代或卤素-、C1-C4-烷基-或C1-C4-烷氧基-取代的苯基取代的；或者是含有总计8-10个环成员的杂二环基团，其中1-5优选1-2个成员是选自B、N、O和S的相同或不同杂原子，并且其中0-2个成员是基团–C(O)-，该二环基团是未取代的或被卤素、氰基、羟基、C1-C4-烷基或C1-C4-卤代烷基取代的；
R2是H或–S(O2)-T；
T是C1-C6-烷基，其是未取代的或被卤素、三甲基硅烷基、C3-C6-环烷基、羧基或C1-C4-烷氧基羰基取代；C3-C6-环烷基；C6-C12-二碳环基；苯基，其是未取代的或被卤素、氰基、硝基、C1-C4-烷基、C1-C4-卤代烷基或C1-C4-烷氧基取代的；5-或6元杂芳基，其是未取代的或被卤素、氰基、硝基、C1-C4-烷基、C1-C4-卤代烷基或C1-C4-烷氧基取代的；含有选自N、O、S和S(O2)的1-3个相同或不同杂原子的5-或6-元杂环烷基，其是未取代的或被C1-C4-烷基、C1-C2-烷氧基羰基或苄氧基羰基取代的；基团氨基；或N-单-或N,N-二-C1-C4-烷基氨基；
R3是C1-C4-烷基，未取代或卤素-、C1-C4-烷基-或C1-C4-卤代烷基-取代的苯基，未取代或卤素-、C1-C4-烷基-或C1-C4-卤代烷基-取代的吡啶基，C1-C4-烷氧基羰基甲基或吗啉-4-基-羰基甲基；
R0是H或羟基；和
Y是
(i)苯基或苯基氨基，其被选自以下的一个或多个相同或不同基团取代：卤素；C1-C6-烷基；C1-C6-卤代烷基；C3-C6-环烷基；C3-C6-卤代环烷基；羟基；C1-C6-烷氧基；C1-C6-卤代烷氧基；C1-C6-烷硫基；C1-C6-卤代烷硫基；C1-C6-烷基-亚磺酰基；C1-C6-卤代烷基亚磺酰基；C1-C6-烷基磺酰基；C1-C6-卤代烷基磺酰基；SF5；氨基；N-单-或N,N-二-C1-C6-烷基氨基；三-C1-C4-烷基硅烷基；C1-C6-烷氧基羰基；氨基羰基；N-单-或N,N-二-C1-C6-烷基氨基羰基；氨基磺酰基；N-单-或N,N-二-C1-C6-烷基氨基磺酰基；N-C1-C6-烷基磺酰基氨基；C1-C6-烷氧基羰基氨基；N-C1-C4-烷基-N-C1-C6-烷氧基羰基氨基；氰基；硝基；和未取代的或卤素-、C1-C4-烷基-、C1-C4-卤代烷基-、C1-C4-烷氧基-、C1-C4-卤代烷氧基-、氨基-、氰基-或硝基-取代的C3-C6-杂环基；或者是
(ii)5-或6元杂芳基或杂芳基氨基，其各自还是未取代的或被以下基团取代：卤素、氰基、硝基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-烷氧基羰基、C2-C4-烷酰基、或苯基或者苯磺酰基，其各自是未取代的或被卤素、氰基、硝基甲基或甲氧基取代的；或者是
(iii)苯甲酰基或者5-或6元杂芳基羰基，其各自是未取代的或者被卤素、氰基、硝基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-烷氧基羰基、C2-C4-烷酰基或苯基取代的；或者是
(iv)C6-C12-二碳环基团；或者是
(v)含有总计8-10个环成员的杂二环基团，其中1-5优选1-2个成员是选自B、N、O和S的相同或不同杂原子，并且其中0-2个成员是基团–C(O)-，该二环基团是未取代的或被卤素、氰基、羟基、C1-C4-烷氧基、C1-C4-烷基或C1-C4-卤代烷基取代的；或者是
(vi)基团–H2C-C(O)-NH-R4，其中R4是C1-C4-卤代烷基、C2-C3-炔基或者氰基-C1-C4-烷基；或者
R0和Y与他们连接的N-原子一起形成哌啶基或哌嗪基基团，其被下述基团取代：C1-C4-烷基、C1-C4-烷氧基、未取代的或卤素-、C1-C4-烷基-、C1-C4-卤代烷基-、氨基-和/或C1-C4-烷氧基-取代的苯基或苯甲酰氨基、或者未取代的或C1-C4-烷基-、C1-C4-卤代烷基-、C3-C6-环烷基-或卤素-取代的吡啶基或嘧啶基；
前提是
(i)如果T是CH3，则A和Y中的至少一个一定不是苯基基团；和
(ii)如果A是C1-C6-烷基或C1-C6-卤代烷基，则T是上述未取代或取代的C1-C6-烷基。
本发明还提供含有式(I)化合物或者其盐或对映异构体以及至少一种载体例如表面活性剂、固体稀释剂和/或液体稀释剂的组合物。
在一实施方案中，本发明还提供用于控制寄生虫特别是体内寄生虫的组合物，其含有生物学有效量的式(I)化合物或其盐，以及至少一种选自表面活性剂、固体稀释剂和液体稀释剂的其他组分，所述组合物还任选地包含生物学有效量的至少一种其他药学或兽医学的活性化合物或物质。
本发明还提供用于控制寄生虫的方法，其包含使寄生虫或其环境与药学或兽医学有效量的式(I)化合物、其对映异构体或盐(例如作为文中所述的组合物)接触。本发明还涉及所述方法，其中寄生虫或其环境与含有药学或兽医学有效量的式(I)化合物、其对映异构体或盐，以及至少一种选自表面活性剂、固体稀释剂和液体稀释剂的其他组分的组合物接触，所述组合物还任选地包含药学或兽医学有效量的至少一种其他药学或兽医学活性化合物或物质。
本发明还提供保护动物免于寄生害虫的方法，所述方法包含向动物施用杀寄生虫有效量的式(I)化合物、其对映异构体或盐。
发明详述
在上文中，单独或在复合词语例如“烷硫基”、“卤代烷硫基”、“卤代烷基”、“N-烷基氨基”、“N,N-二-烷基氨基”等中所用的术语“烷基”包括直链或支链烷基例如甲基、乙基、正丙基、异丙基、正-、异-、仲-或叔-丁基或者不同的戊基或己基异构体。
单独或在复合词语例如“卤代烷氧基”、“烷氧基羰基”中所用的术语“烷氧基”包括例如甲氧基、乙氧基、正丙氧基、异丙氧基和不同的丁氧基、戊氧基或己氧基异构体。“烷硫基”包括支链或直链烷硫基基团例如甲硫基、乙硫基，以及不同的丙硫基、丁硫基、戊硫基和己硫基异构体。
“烷基亚磺酰基”包括烷基亚磺酰基基团的两种对映异构体。“烷基亚磺酰基”的示例包括CH3S(O)-、CH3CH2S(O)-、CH3CH2CH2S(O)-、(CH3)2CHS(O)-，以及不同的丁基亚磺酰基、戊基亚磺酰基和己基亚磺酰基异构体。
“烷基羰基”指键合至C(＝O)基团的直链或支链烷基基团。“烷基羰基”的示例包括CH3C(＝O)-、CH3CH2CH2C(＝O)-和(CH3)2CHC(＝O)-。“烷氧基羰基”的示例包括CH3OC(＝O)-、CH3CH2OC(＝O)、CH3CH2CH2OC(＝O)-、(CH3)2CHOC(＝O)-和不同的丁氧基-或戊氧基羰基异构体，例如叔-丁氧羰基(Boc)。“烷氧基羰基氨基”的示例包括叔-叔丁氧羰基氨基，“N-烷氧基羰基”的示例包括N-叔-丁氧羰基，并且“N-烷基氨基”的示例包括N-甲基氨基。“N-单-或N,N-二-烷基氨基羰基”的示例包括N-甲基氨基羰基、N-乙基氨基羰基、N-甲基-N-乙基氨基羰基、N,N-二-甲基氨基羰基或N,N-二-乙基氨基羰基。“烷基羰基氨基”的示例包括甲基羰基氨基或乙基羰基氨基。
“烷基磺酰基”的示例包括CH3S(O)2-、CH3CH2S(O)2-、CH3CH2CH2S(O)2-、(CH3)2CHS(O)2-和不同的丁基磺酰基、戊基磺酰基和己基磺酰基异构体。“N-单-或N,N-二-烷基氨基磺酰基”的示例包括N-甲基氨基磺酰基、N-乙基氨基磺酰基、N-甲基-N-乙基氨基磺酰基、N,N-二-甲基氨基磺酰基或N,N-二-乙基氨基磺酰基。“烷基磺酰基氨基”的示例包括甲基磺酰氨基或乙基磺酰氨基。
“环烷基”包括例如环丙基、环丁基、环戊基和环己基。术语“烷基环烷基”指环烷基基团上有烷基取代，并包括例如乙基环丙基、异丙基环丁基、3-甲基环戊基和4-甲基环己基。
C6-C12-二碳环基的示例是基团(+)-或(-)-樟脑(1,7,7-三甲基二环[2.2.1]-庚烷-2-酮)、基团基团或茚满基。
单独或在复合词语例如“卤代烷基”中的术语“卤素”包括氟、氯、溴或碘。此外，当在复合词语例如“卤代烷基”中使用时，所述烷基可以是部分或完全被卤素原子取代的，所述卤原子可以是相同或不同的。“卤代烷基”的示例包括F3C-、ClCH2-、CF3CH2-和CF3CCl2-。类似于术语“卤代烷基”那样定义术语“卤代环烷基”、“卤代烷氧基”、“卤代烷硫基”等。“卤代烷氧基”的示例包括CF3O-、CF3CF2-O-、CF3CH2O-、CCl3CH2O-、CF3CHFCF2O-和HCF2CH2CH2O-。“卤代烷硫基”的示例包括CCl3S-、CF3S-、CCl3CH2S-和ClCH2CH2CH2S-。“卤代烷基亚磺酰基”的示例包括CF3S(O)-、CCl3S(O)-、CF3CH2S(O)-和CF3CF2S(O)-。“卤代烷基磺酰基”的示例包括CF3S(O)2-、CCl3S(O)2-、CF3CH2S(O)2-和CF3CF2S(O)2-。
通过前缀“Ci-Cj”表示取代基中碳原子的总数，其中i和j是整数。例如，C1-C4烷基磺酰基指甲基磺酰基至丁基磺酰基。
当化合物被具有下标(下标表示所述取代基的数目可超过1)的取代基取代时，所述取代基(当其超过1时)独立选自所定义的取代基的组，例如(R2)n，n是1或2。
“芳香的”表示各个环原子基本处于相同平面，并具有垂直于环平面的ap-轨道，并且其中(4n+2)π电子(其中n是正整数)是与环相关的，以符合规则。
术语“杂环基”、“杂环”指其中形成环骨架的至少一个原子不是碳(例如氮、氧、硫或基团S(O)或S(O2))的环。通常，杂环含有不超过4个氮，不超过2个氧和不超过2个硫。此外，杂环可含有基团–C(O)-、-S(O)-或–S(O2)-。除非另外说明，杂环可以是饱和的、部分不饱和的或完全不饱和的环。当完全不饱和杂环满足规则时，则还将所述环称作“杂芳香环”或“杂芳基”取代基。除非另外说明，杂环和环系可通过任何可用的碳或氮经替换所述碳或氮上的氢而连接。
单独或在复合词语例如杂环氧基中的术语杂环基可以是例如5-或6-元杂环基团，其含有选自B、N、O和S的1-4个优选1-3个相同或不同杂原子，其是未取代或取代的。杂环基的适当取代基的示例是卤素、C1-C6-烷基、C1-C6-卤代烷基、C3-C6-环烷基、C3-C6-卤代环烷基、羟基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C1-C6-烷硫基、C1-C6-卤代烷硫基、C1-C6-烷基亚磺酰基、C1-C6-卤代烷基亚磺酰基、C1-C6-烷基磺酰基、C1-C6-卤代烷基磺酰基、氰基、硝基、氨基、N-单-或N,N-二-C1-C4-烷基氨基、C1-C6-烷氧基羰基、磺酰氨基、N-单-或N,N-二-C1-C4-烷基磺酰氨基、C1-C6-烷基羰基氨基、N-单-或N,N-二-C1-C6-烷基氨基羰基、C2-C6-烷酰基或苯基，其是未取代的或被卤素、C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、氰基或硝基取代的。
术语杂环基可指例如5-或6-元杂芳基基团，其含有选自N、O和S的1-4个优选1-3个相同或不同杂原子，其是未取代或被上文为杂环基定义的一个或多个取代基取代的。杂芳基基团优选被上文定义的0-3个特别是0、1或2个取代基取代。
单独的或术语例如杂芳基氨基或杂芳基羰基中的术语5-或6-元杂芳基可包括例如噻吩基、吡咯基、吡唑基、呋喃基、唑基、噻唑基、异噻唑基、噻二唑基、吡啶基、嘧啶基或噻嗪基基团，其各自是未取代的或者被例如卤素、氰基、硝基、C1-C2-烷基、C1-C2-卤代烷基、C3-C6-环烷基、C1-C4-烷氧基、C2-C4-烷酰基、C1-C4-烷氧基羰基或者未取代或取代的苯基取代的。
术语杂环基还可以指含有选自B、N、O和S的1-3个相同或不同杂原子的3-6-元杂环烷基基团，其是未取代的或进一步被上文为杂环基定义的一个或多个取代基取代的。亚杂环烷基(heterocycloalkylene)优选被上文定义的0-3个特别是0、1或2个取代基取代。示例是四氢呋喃基、吡咯烷基、吗啉基、哌啶基、哌嗪基或二氧硼杂环戊烷基，其各自是未取代或被卤素、C1-C2-烷基、C1-C2-卤代烷基或C1-C2-烷氧基取代的。
杂环氧基的示例是2-、3-或4-吡啶基氧基或嘧啶-4-基氧基，其各自是未取代或被卤素、C1-C2-烷基、C3-C6-环烷基、C1-C2-卤代烷基或C1-C2-烷氧基取代的。
杂二环基团的示例是苯并噁唑基、苯并噻唑基、四氢-苯并噻唑基、吲哚基、苯并咪唑基、苯并吡唑基、5,6-二氢-4H-环戊二烯并[b]噻吩-2-基、亚甲二氧苯基、苯并氧硼杂环戊基(benzooxaboronyl)、喹啉基(chinolinyl)、三唑并嘧啶酮基例如1,2,3-三唑并[4,5-d]嘧啶-7-酮-5-基或邻苯二甲酰肼基(phthalhydrazidyl)，其各自可以是未取代或被例如卤素、氰基、C1-C4-烷基、C1-C2-卤代烷基、羟基或C1-C2-烷氧基取代的。
对于式(I)化合物中包含的变量，应用下述含义和优选。
如果A是苯基基团，则变量n优选是1。如果A不同于苯基基团，例如如果A是C1-C6-烷基、C1-C6-卤代烷基、C3-C6-环烷基；C3-C6-卤代环烷基；5-或6-元杂环烷基基团、杂芳基或杂二环基团，则变量n优选是0。
苯基基团A的优选取代基是卤素；C1-C4-烷基；C1-C4-卤代烷基；氨基；C1-C4-烷氧基；C1-C4-卤代烷氧基；C1-C4-卤代烷硫基；C1-C4-烷基磺酰基；C1-C4-卤代烷基磺酰基；三-C1-C2-烷基硅烷基；C1-C4-烷氧基羰基；N-单-或N,N-二-C1-C4-烷基氨基羰基；氨基磺酰基；N-单-或N,N-二-C1-C4-烷基氨基磺酰基；N-C1-C2-烷基-N-C1-C4-烷氧基羰基氨基；氰基；硝基；或包含选自O、S和N的1个或2个相同或不同杂原子的5-或6-元杂环烷基，其是未取代的或被卤素、C1-C2-烷基、C1-C2-卤代烷基或C1-C2-烷氧基取代的。
苯基基团A的更优选取代基是卤素；C1-C2-烷基；C1-C4-卤代烷基；氨基；C1-C4-烷氧基；C1-C4-卤代烷氧基；C1-C4-烷基磺酰基；C1-C4-卤代烷基磺酰基；三甲基硅烷基；C1-C4-烷氧基羰基；N,N-二-C1-C2-烷基氨基羰基；氨基磺酰基；N,N-二-C1-C2-烷基氨基磺酰基；N-C1-C2-烷基-N-C1-C4-烷氧基羰基氨基；氰基；硝基；或者杂环烷基基团，其选自四氢呋喃基、吡咯烷基、吗啉基和哌啶基。
苯基基团A的尤其优选的取代基是卤素、C1-C2-烷基、C1-C2-卤代烷基、C1-C2-烷氧基、C1-C2-卤代烷氧基或氰基，并尤其是氯、氟或CF3。
具体的优选苯基基团A是2-、3-或4-Cl-苯基、4-CF3-苯基、3,5-二-Cl-苯基、3,5-二-CF3-苯基、2,4,6-三-Cl-苯基、3,4,5-三-Cl-苯基、2-Cl-4-CF3-苯基、2-CF3-4-Cl-苯基或者2,6-二-Cl-4-CF3-苯基，特别是4-Cl-苯基。
作为C1-C6-烷基，A优选是C1-C4-烷基。作为卤代烷基，A优选是C1-C2-卤代烷基，特别是CF3。
作为5-或6-元杂环烷基，A优选是吡咯烷基、哌嗪基、吗啉基或二氧硼杂环戊烷基，其各自是未取代的或被甲基取代的。
作为杂芳基，A优选是吡咯基、吡唑基、三唑基、噻吩基、噻嗪基、噻唑基、吡啶基或嘧啶基，其各自是未取代的或被卤素、氰基、C1-C2-烷基、C1-C2-烷氧基、C1-C2-卤代烷基、乙酰基、丙酰基、苯基或吗啉-4-基-甲基取代的。作为杂芳基，A的特别优选的含义是2-、3-或4-吡啶基，其是未取代的或被卤素、氰基、C1-C2-烷氧基、乙酰基或丙酰基取代的；嘧啶基，其是未取代的或被卤素或乙酰基取代的；1,2,4-三唑-5-基，其是未取代的或被苯基取代的；噻吩基，其是未取代的或被卤素、乙酰基或吗啉-4-基-甲基取代的；吡唑-1-基或-5-基，其各自是未取代的或被甲基取代的；或者噻嗪-4-基。
作为杂二环基团，A优选是吲哚基、苯并吡唑基或苯并噻唑，其各自是未取代的或被甲基取代的。
根据本发明的优选实施方案，A是C1-C4-烷基；C1-C2-卤代烷基；杂环烷基，其选自吡咯烷基、哌嗪基、吗啉基和二氧硼杂环戊烷基，其各自是未取代的或被甲基取代的；杂芳基，其选自吡咯基、吡唑基、三唑基、噻吩基、噻嗪基、噻唑基、吡啶基和嘧啶基，其各自是未取代的或被卤素、氰基、C1-C2-烷基、C1-C2-烷氧基、C1-C2-卤代烷基、乙酰基、丙酰基、苯基或吗啉-4-基-甲基取代的；或者杂二环基团，其选自吲哚基、苯并吡唑基和苯并噻唑，其各自是未取代的或被甲基取代的。
变量R2优选是H。
作为烷基基团，T优选是C1-C4-烷基，其是未取代的或被卤素、环丙基、环己基、三甲基硅烷基、羧基或C1-C2-烷氧基羰基取代的。作为烷基基团，T特别优选的含义是C1-C4-烷基；C1-C3-卤代烷基，特别是CF3、-CH2-CF3或-CH2-CH2-CF3；三甲基硅烷基-C1-C2-烷基；C1-C2-烷氧基羰基甲基；羧基甲基；或环己基甲基；尤其是甲基。
作为C3-C6-环烷基，T优选是环丙基或环己基。
作为二碳环基，T是例如二环亚烷基(bicycloalkylene)或二环亚烷酮(bicycloalkylenone)基团，例如1,7,7-三甲基二环[2.2.1]庚基或1,7,7-三甲基二环[2.2.1]庚烷-2-酮-基((+)-或(-)-樟脑)。
作为苯基基团，T优选是苯基，其是未取代的或被氟、氯、甲基、甲氧基、CF3或硝基取代的。
作为杂芳基，T优选是吡啶基、噻吩基或嘧啶基。
作为杂环烷基，T优选是哌啶基、哌嗪基、四氢吡喃基、吗啉基、硫代吗啉基或硫代吗啉-4-基-1,1-二氧化物，其各自是未取代的或被甲基或苄氧基羰基取代的。特别优选的杂环基基团T是1-甲基哌嗪-4-基、1-(苄氧基羰基)-哌嗪-4-基、四氢-2H-吡喃-4-基或硫代吗啉-4-基-1,1-二氧化物。
R3优选是甲基、卤代苯基、三氟甲基吡啶基、叔-丁氧羰基甲基或吗啉-4-基氧羰基甲基。
T优选是C1-C4-烷基；C1-C3-卤代烷基；三甲基硅烷基-C1-C2-烷基；C1-C2-烷氧基羰基甲基；羧基甲基；环己基甲基；C3-C6-环烷基；1,7,7-三甲基二环[2.2.1]庚基或1,7,7-三甲基二环[2.2.1]庚烷-2-酮-基((+)-或(-)-樟脑)；苯基，其是未取代的或被氟、氯、甲基、甲氧基、CF3或硝基取代的；吡啶基、噻吩基或嘧啶基；杂环烷基，其选自哌啶基、哌嗪基、四氢吡喃基、吗啉基、硫代吗啉基或硫代吗啉-4-基-1,1-二氧化物，其各自是未取代的或被甲基或苄氧基羰基取代的；或者基团其中R3是甲基、卤代苯基、三氟甲基吡啶基、叔-丁氧羰基甲基或吗啉-4-基氧羰基甲基。
R0优选是H。
苯基或苯基氨基基团Y的优选取代基是卤素；C1-C4-烷基；C1-C4-卤代烷基；C3-C6-环烷基；C1-C4-烷氧基；C1-C4-卤代烷氧基；C1-C4-卤代烷硫基；SF5；N,N-二-C1-C4-烷基氨基-C1-C4-烷基氨基羰基；N-C1-C4-烷基磺酰基氨基；氰基；硝基；羟基；B(OH)2或甲基磺酰氨基。
苯基或苯基氨基基团Y的更优选的取代基是卤素；C1-C2-烷基；C1-C3-卤代烷基；C1-C2-烷氧基；C1-C3-卤代烷氧基；C1-C2-卤代烷硫基；SF5；氰基；硝基；羟基或甲基磺酰氨基。
苯基或苯基氨基基团Y的特别优选的取代基是卤素、甲基、C1-C3-卤代烷基、甲氧基、C1-C3-卤代烷氧基、SCF3、SF5、氰基、硝基或羟基，并尤其是卤素或CF3。
具体的优选的苯基基团Y是3,4,5-三氯苯基、3,5-二-三氟甲基-4-氯苯基和3,5-二-三氟甲基苯基。
具体的优选的苯基氨基基团Y是苯基氨基，其是被氯、溴、甲基三氟甲基、甲氧基、氰基或硝基取代的。
杂芳基基团Y是例如吡咯基、吡唑基、唑基、噻吩基、噻唑基、异噻唑基、噻二唑基、吡啶基或嘧啶基，其各自是未取代的或被下列基团取代：卤素、氰基、硝基、C1-C4-烷基、C1-C2-卤代烷基、C1-C2-烷氧基、C1-C2-烷氧基羰基或苯基或苯磺酰基，其各自是未取代的或被卤素、氰基、硝基、甲基或甲氧基取代的。
杂芳基基团Y优选是2-、3-或4-吡啶基，其是未取代的或被卤素、C1-C4-烷基或C1-C2-烷氧基取代的；2-噻吩基，其是未取代的或被C1-C2-烷基或C1-C2-烷氧基羰基取代的；2-噻唑基，其是未取代的或被下列基团取代：卤素、氰基、硝基、C1-C2-烷基、C1-C2-卤代烷基、C1-C2-烷氧基羰基或者苯基或苯磺酰基，其各自依次是未取代的或被卤素、氰基、硝基或甲基取代的；5-异噻唑基，其是未取代的或被卤素或甲基取代的；2-唑基，其是未取代的或被C1-C2-烷基或C1-C2-卤代烷基取代的；或者1,3,4-噻二唑-5-基，其是未取代的或被C1-C2-烷基或C1-C2-卤代烷基取代的。
杂芳基氨基基团Y优选是2-、3-或4-吡啶基氨基，其是未取代的或被卤素、C1-C4-烷基或C1-C2-烷氧基取代的。
苯甲酰基或杂芳基羰基基团Y优选是苯甲酰基，其是未取代的或被卤素取代的；或者2-、3-或4-吡啶基羰基，其是未取代的或被卤素或C1-C4-烷基取代的。
优选的二碳环基团Y优选是基团基团或茚满基。
优选的杂二环基团Y是苯并噻唑基、吲哚基、喹啉基、亚甲二氧基苯基、苯并氧硼杂环戊基、三唑并嘧啶酮基或邻苯二甲酰肼基，其各自是未取代的或被卤素、C1-C4-烷基、C1-C2-卤代烷基、C1-C4-烷氧基或羟基取代的。
变量R4优选是丙炔基、2,2,2-三氟乙基或氰基甲基。
因此，优选的基团Y是(i)苯基或苯基氨基，其是被卤素、C1-C2-烷基、C1-C3-卤代烷基、C1-C2-烷氧基、C1-C3-卤代烷氧基、C1-C2-卤代烷硫基、SF5、氰基、硝基、羟基或甲基磺酰氨基取代的；(iia)选自以下的杂芳基：2-、3-或4-吡啶基，其是未取代的或被卤素、C1-C4-烷基或C1-C2-烷氧基取代的；2-噻吩基，其是未取代的或被C1-C2-烷基或C1-C2-烷氧基羰基取代的；2-噻唑基，其是未取代的或被以下基团取代的：卤素、氰基、硝基、C1-C2-烷基、C1-C2-卤代烷基、C1-C2-烷氧基羰基或者苯基或苯磺酰基，它们各自依次是未取代的或被卤素、氰基、硝基或甲基取代的；5-异噻唑，其是未取代的或被卤素或甲基取代的；2-唑基，其是未取代的或被C1-C2-烷基或C1-C2-卤代烷基取代的；或1,3,4-噻二唑-5-基，其是未取代的或被C1-C2-烷基或C1-C2-卤代烷基取代的；(iib)杂芳基氨基，其选自2-、3-或4-吡啶基氨基，其是未取代的或被卤素、C1-C4-烷基或C1-C2-烷氧基取代的；(iii)苯甲酰基，其是未取代的或被卤素取代的，或2-、3-或4-吡啶基羰基，其是未取代的或被卤素或C1-C4-烷基取代的；(iv)二碳环基团，其选自基团基团和茚满基；(v)杂二环基团，其选自苯并噻唑基、吲哚基、喹啉基、亚甲二氧苯基、苯并氧硼杂环戊基、三唑并嘧啶酮基和邻苯二甲酰肼基，其各自是未取代的或被卤素、C1-C4-烷基、C1-C2-卤代烷基、C1-C4-烷氧基或羟基取代的；或者(vi)基团–H2C-C(O)-NH-R4，其中R4是丙炔基、2,2,2-三氟乙基或氰基甲基。
如果R0和Y与其连接的N-原子一起形成哌啶基或哌嗪基基团，所述哌啶基或哌嗪基基团优选被下述基团取代：甲基；甲氧基；卤素-、氨基-、甲氧基-或三氟甲基-取代的苯基或苯甲酰氨基；或者卤素-、三氟甲基-和/或环丙基-取代的吡啶基或嘧啶基。
本发明的一实施方案涉及式(Ia)化合物，
其中n具有上文赋予的含义，包括优选项，Y’是苯基，其如上所述被取代，包括优选项；并且A’是C1-C6-烷基；C1-C6-卤代烷基；C3-C6-环烷基；C3-C6-卤代环烷基；含有选自B、N、O和S的1-3个相同或不同杂原子的5-或6-元杂环烷基，其是未取代的或进一步被卤素、C1-C4-烷基或C1-C4-烷氧基取代的；杂芳基，其是未取代的或进一步被下述基团取代：卤素、氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C1-C4-烷酰基、5-或6-元杂环烷基-C1-C2-烷基、或者未取代的或卤素-、C1-C4-烷基-或C1-C4-烷氧基-取代的苯基；或者是含有总计8-10个环成员的杂二环基团，其中1-5个优选1或2个成员是选自B、N、O和S的相同或不同杂原子，并且其中0-2个成员是基团–C(O)-，该二环基团是未取代的或被卤素、氰基、羟基、C1-C4-烷氧基、C1-C4-烷基或C1-C4-卤代烷基取代的。
如下式(Ia)化合物是尤其优选的，其中Y’是苯基，其是被选自卤素或CF3的2个或3个相同或不同基团取代的；并且A’是C1-C4-烷基；CF3；吡咯烷基、哌嗪基、吗啉基或二氧硼杂环戊烷基，其各自是未取代的或被甲基取代的；吡咯基、吡唑基、三唑基、噻吩基、噻嗪基、噻唑基、吡啶基或嘧啶基，其各自是未取代的或被卤素、氰基、C1-C2-烷基、C1-C2-烷氧基、C1-C2-卤代烷基、乙酰基、丙酰基、苯基或吗啉-4-基-甲基取代的；或者吲哚基、苯并吡唑基或苯并噻唑基，其各自是未取代的或被甲基或甲氧基取代的；并且n是0或1，特别是1。
本发明的另一优选实施方案涉及式(Ib)化合物
其中A是苯基，其是未取代的或如上所述取代的，包括优选项，Y是苯基，其是如上所述取代的，包括优选项，T是C2-C6-烷基，其是未取代的或被卤素、三甲基硅烷基、C3-C6-环烷基、羧基或C1-C4-烷氧基羰基取代的；C3-C6-环烷基；C6-C12-二碳环基；苯基，其是未取代的或被卤素、氰基、硝基、C1-C4-烷基、C1-C4-卤代烷基或C1-C4-烷氧基取代的；5-或6元杂芳基，其是未取代的或进一步被卤素、C1-C4-烷基或C1-C4-烷氧基取代的；氨基；N-单-或N,N-二-C1-C4-烷基氨基；含有选自N、O、S和S(O2)的1-3个相同或不同杂原子的5-或6-元杂环烷基，其是未取代的或进一步被C1-C4-烷基取代的；或者基团并且R3是C1-C4-烷基、未取代或卤素-、C1-C4-烷基-或C1-C4-卤代烷基-取代的苯基、未取代或卤素-、C1-C4-烷基-或C1-C4-卤代烷基-取代的吡啶基、C1-C4-烷氧基羰基甲基或吗啉-4-基-羰基甲基。
优选的实施方案涉及式(Ib)化合物，其中A是苯基，其是未取代的或者优选被氯、氟或CF3单-取代的，Y是苯基，其是被选自卤素或CF3的2个或3个相同或不同基团取代的，并且T是C2-C4-烷基，其是未取代的或被卤素、环丙基、环己基、三甲基硅烷基、羧基或C1-C2-烷氧基羰基取代的；环丙基或环己基；基团(+)-或(-)-樟脑；苯基，其是未取代的或被氟、氯、甲基、甲氧基、CF3或硝基取代的；或者吡啶基、噻吩基或嘧啶基；哌啶基、哌嗪基、四氢吡喃基、吗啉基、硫代吗啉基或硫代吗啉-4-基-1,1-二氧化物，其各自是未取代的或被甲基或苄氧基羰基取代的。
本发明的另一优选实施方案涉及式(Ic)化合物
其中A是苯基，其是未取代的或如上所述取代的，包括优选项，R0是H或羟基；并且Y”是
(i)5-或6元杂芳基或杂芳基氨基，其各自是未取代的或被下列基团取代：卤素、氰基、硝基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-烷氧基羰基、C1-C4-烷酰基或苯基或苯磺酰基，它们各自是未取代的或被卤素、氰基、硝基甲基或甲氧基取代的；或者是
(ii)苯甲酰基或者5-或6元杂芳基羰基，其各自是未取代的或被卤素、氰基、硝基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-烷氧基羰基、C1-C4-烷酰基或苯基取代的；或者是
(iii)C6-C12-二碳环基团；或者是
(iv)含有总计8-10个环成员的杂二环基团，其中1-5个优选1-2个是选自B、N、O和S的相同或不同杂原子，并且其中0-2个是基团–C(O)-，所述二环基团是未取代的或被卤素、氰基、羟基、C1-C4-烷基、C1-C4-烷氧基或C1-C4-卤代烷基取代的；或者是
(v)基团–H2C-C(O)-NH-R4，其中R4是C1-C4-卤代烷基、C2-C3-炔基或氰基-C1-C4-烷基；或者R0和Y与它们连接的N-原子一起形成哌啶基或哌嗪基基团，其被下述基团取代：C1-C4-烷基、C1-C4-烷氧基、未取代或卤素-、C1-C4-烷基-、卤代-C1-C4-烷基-、氨基-和/或C1-C4-烷氧基-取代的苯基或苯甲酰氨基、或者未取代或C1-C4-烷基-、C1-C4-卤代烷基-、C3-C6-环烷基-或卤素-取代的吡啶基或嘧啶基。
关于式(Ic)化合物的优选实施方案，A是苯基，其是未取代的或者优选被氯、氟或CF3单-取代的；R0是H，并且Y”是
(i)2-、3-或4-吡啶基，其是未取代的或者被卤素、C1-C4-烷基或C1-C2-烷氧基取代的；2-噻吩基，其是未取代的或者被C1-C2-烷基、C1-C2-烷氧基羰基取代的；2-噻唑基，其是未取代的或者被下述基团取代：卤素、氰基、硝基、C1-C2-烷基、C1-C2-卤代烷基、C1-C2-烷氧基羰基或苯基或苯磺酰基，它们各自是未取代的或被卤素、氰基、硝基或甲基取代的；5-异噻唑基，其是未取代的或者被卤素或甲基取代的；2-唑基，其是未取代的或者被C1-C2-烷基或C1-C2-卤代烷基取代的；或者1,3,4-噻二唑-5-基，其是未取代的或者被C1-C2-烷基或C1-C2-卤代烷基取代的；2-、3-或4-吡啶基氨基，其是未取代的或被卤素、C1-C4-烷基或C1-C2-烷氧基取代的；或者
(ii)苯甲酰基，其是未取代的或者被卤素取代，或者2-、3-或4-吡啶基羰基，其是未取代的或者被卤素或C1-C4-烷基取代的；或者
(iii)基团基团或茚满基；或者
(iv)苯并噻唑基、吲哚基、喹啉基、亚甲二氧苯基、苯并氧硼杂环戊基、三唑并嘧啶酮基或邻苯二甲酰肼基，其各自是未取代的或者被卤素、C1-C4-烷基、C1-C2-卤代烷基或羟基取代的；
(v)基团–H2C-C(O)-NH-CH2-C≡CH、–H2C-C(O)-NH-CH2-CN或–H2C-C(O)-NH-CH2-CF3；或者R0和Y与它们连接的N-原子一起形成哌啶基或哌嗪基基团，其被下述基团取代：甲基；甲氧基；卤素-、氨基-、甲氧基-或三氟甲基-取代的苯基或苯甲酰氨基；或者卤素-、三氟甲基-和/或环丙基-取代的吡啶基或嘧啶基。
可以按照已知方式生产式(I)化合物的盐。例如，通过用适宜的酸或适宜的离子交换试剂处理可得到酸加成盐，和通过用适宜的碱或适宜的离子交换试剂处理可得到与碱形成的盐。
可以通过常用方式将式(I)化合物的盐转化成游离化合物，例如通过用适宜的碱性组合物或适宜的离子交换试剂处理转化酸加成盐，和例如通过用适宜的酸或适宜的离子交换试剂处理转化与碱形成的盐。
可以按照已知方式将式(I)化合物的盐转化成式(I)化合物的其它盐；例如，酸加成盐可以如下转化为其它酸加成盐：例如通过用适宜的酸的金属盐如钠、钡或银盐例如乙酸银在适宜的溶剂中处理无机酸的盐如盐酸盐，在所述溶剂中，所产生的无机盐如氯化银不溶并且因此从反应混合物中沉淀出来。
根据方法和/或反应条件的不同，可以得到游离形式或盐形式的具有成盐特性的式(I)化合物。
式(I)化合物还可以以其水合物的形式得到和/或还可以包括例如当必要时对于以固体形式存在的化合物的结晶使用的其它溶剂。
如上所述，式(I)化合物可以任选作为光学异构体和/或几何异构体或其混合物存在。本发明涉及纯的异构体和所有可能的异构体混合物，并且在上下文中被理解为如此，即使没有在每种情况中具体提到立体化学详情。
可通过所述方法或其它方法得到的式(I)化合物的非对映异构体混合物可以基于其成分的物化差异按照已知方式分离成纯的非对映异构体，例如通过分步结晶、蒸馏和/或色谱法。
可以通过已知方法将可相应获得的对映异构体混合物分离成纯的异构体，例如通过从光学活性的溶剂中重结晶、通过手性吸附剂色谱法、例如采用醋酸纤维素的高压液相色谱法(HPLC)、借助于适当的微生物、通过用特异性固定化酶裂解、经由包合化合物的形成、例如采用手性冠醚形成包合化合物(由此仅一种对映异构体被复合)来进行。
其中n是0的式(I)化合物可例如通过在钯催化剂存在下，使式(II)化合物，
其中R0、R2、T和Y各自同上文所定义的，并且LG是离去基团例如卤素如溴，
与式(III)化合物反应来制备
其中A是上文所定义的。称作Suzuki反应的该钯-催化的碳-碳键形成反应的详情可从有机化学教科书了解。
式(II)化合物是已知的或者可根据已知方法制备，例如通过使式(IV)化合物，
与式(V)化合物反应
其中LG’是离去基团，例如卤素、C1-C2-烷氧基或羟基，并且其他变量各自具有上文所述的含义。根据有机化学教科书，羧酸或其衍生物与胺的酰胺形成是已知的。式(IV)化合物是已知的或者可根据已知方法制备，例如通过已知方式使相应胺与甲烷磺酰氯反应。式(III)和(V)化合物是市售的已知化合物。
其中n是0的一些式(I)化合物也可例如通过利用苯环的亲电取代，式(IIa)化合物
其中R0、R2、T和Y各自同上文所定义的，并且LG是离去基团例如卤素如溴或氯，
与式(IIIa)化合物反应制备，
其中A*是杂环基团A，并且H-原子连接至杂原子例如N或O。式(IIa)化合物可以类似于上述式(II)化合物那样获得。
其中n是1的式(I)化合物可例如通过式(VI)化合物，
与式(VII)化合物反应来制备
其中变量是同上文所定义的，随后，还原硝基基团，并使得到的胺进一步与甲烷磺酰氯反应。根据有机化学教科书，这些反应的详情是已知的。类似于式(II)化合物，可制备式(VI)化合物。式(VII)化合物本身是已知的，并且是市售的。
其中n是1的式(I)化合物还可通过式(VIII)化合物
与式(V)化合物的反应制备，
其中变量各自具有上文所定义的含义，随后，还原硝基基团，并使得到的胺进一步与甲烷磺酰氯反应。或者，在与式(V)化合物反应之前，可首先将式(VIII)化合物的硝基基团还原，并将得到的氨基基团与甲烷磺酰氯反应。
可用本身已知的方式制备式(VIII)化合物，例如通过式
(IX)化合物与式化合物反应来制备。
实施例进一步阐明不同合成方法。
根据本发明的式(I)化合物因其广的活性谱而值得关注，它是用于害虫控制、包括特别是控制在温血动物尤其是家畜和宠物中和之上的体内寄生虫、尤其是蠕虫的有价值的活性成分，并且同时被温血动物和鱼良好耐受。
生产性家畜包括哺乳动物例如牛、马、绵羊、猪、山羊、驴、兔、鹿，以及鸟，例如鸡、鹅、火鸡、鸭和外来鸟。
宠物包括例如狗、猫和仓鼠，特别是狗和猫。
本发明的式(I)化合物有效对抗蠕虫，其中体内寄生的线虫和吸虫可能是哺乳动物和家禽的严重疾病的原因。这种适应征的典型线虫有：丝虫科(Filariidae)、丝状科(Setariidae)、血矛线虫属(Haemonchus)、毛圆线虫属(Trichostrongylus)、胃线虫属(Ostertagia)、细颈线虫属(Nematodirus)、古柏线虫属(Cooperia)、蛔虫属(Ascaris)、Bunostonum、结节线虫属(Oesophagostonum)、Charbertia、鞭虫属(Trichuris)、圆线虫属(Strongylus)、毛线线虫属(Trichonema)、网尾线虫属(Dictyocaulus)、毛细线虫属(Capillaria)、异刺线虫属(Heterakis)、弓蛔虫属(Toxocara)、鸡蛔虫属(Ascaridia)、尖尾线虫属(Oxyuris)、钩口线虫属(Ancylostoma)、钩虫属(Uncinaria)、弓蛔线虫属(Toxascaris)和副蛔虫属(Parascaris)。吸虫特别包括Fasciolideae科，尤其是肝片形吸虫(Fasciola hepatica)(liver fluke)。
还令人意外和出人意料地显示本发明的组合物具有对抗对许多活性物质具有抗性的线虫的异常高的效力。这可以在体外通过LDA试验证实。
一些细颈线虫属、古柏线虫属和结节线虫属物种的害虫侵扰宿主动物的肠道，而其它的血矛线虫属和胃线虫属物种寄生于胃部，网尾线虫属物种的那些寄生于肺组织。在内部细胞组织和器官如心脏、血管、淋巴管和皮下组织中可以发现所述科的寄生虫。特别值得注意的寄生虫是犬的恶丝虫Dirofilaria immitis。根据本发明的式(I)化合物对于对抗这些寄生虫是非常有效的。
本发明的式(I)化合物可以控制的害虫还包括来自如下类别的那些：多节绦虫亚纲(Cestoda)(绦虫)，例如中殖孔绦虫科(Mesocestoidae)，尤其是中殖孔绦虫属(Mesocestoides)，特别是线中殖孔绦虫(M.lineatus)；Dipylidiidae，尤其是犬复殖孔绦虫(Dipylidium caninum)，约优克斯绦虫(Joyeuxiella spp.)，特别是Joyeuxiellapasquali，和复孔绦虫(Diplopylidium spp.)，以及带绦虫科(Taeniidae)，尤其是豆状绦虫(Taenia pisiformis)、獐绦虫(Taenia cervi)、羊绦虫(Taenia ovis)、Taneiahydatigena、多头绦虫(Taenia multiceps)、巨颈绦虫(Taenia taeniaeformis)、链形绦虫(Taenia serialis)，以及棘球绦虫(Echinocuccus spp.)，最优选Taneia hydatigena、羊绦虫、多头绦虫、链形绦虫；细粒棘球绦虫(Echinocuccus granulosus)和多房棘球绦虫(Echinococcus multilocularis)。
此外，式(I)化合物还适于控制人的致病寄生虫。其中，在消化道中出现的典型代表有钩口线虫属(Ancylostoma)、板口线虫属(Necator)、蛔虫属(Ascaris)、类圆线虫属(Strongyloides)、毛线虫属(Trichinella)、毛细线虫属(Capillaria)、鞭虫属(Trichuris)和蛲虫属(Enterobius)的那些。本发明的化合物还可以有效地对抗龙线虫(Dracunculus)科的吴策线虫属(Wuchereria)、布鲁丝虫属(Brugia)、盘尾丝虫属(Onchocerca)和罗阿丝虫属(Loa)的寄生虫，还有效地对抗类圆线虫属(Strongyloides)和毛线虫属(Trichinella)的寄生虫，它们特别感染胃肠道。
式(I)化合物的良好杀灭体内寄生虫活性相当于所述体内寄生虫的死亡率为至少50-60％，特别是至少80％，并尤其是至少90％。
根据本发明的式(I)化合物的施用可在治疗上并优选预防上起效。
可以通过例如局部、经口、胃肠道外或皮下，将根据本发明的式(I)化合物应用于待治疗的动物。本发明的优选实施方案涉及用于肠胃外应用特别是口服应用的式(I)化合物。
用于在温血动物上控制线虫/蠕虫的优选的应用形式包括溶液剂；乳剂包括经典乳剂、微乳剂和自乳化组合物(其是无水有机组合物优选油性组合物，一旦加入到动物体，其与体液一起形成乳剂)；混悬剂(灌服剂(drenches))；浇泼(pour-on)制剂；食品添加剂；粉剂；片剂(包括泡腾片)；大丸剂(boli)；胶囊剂包括微囊剂；和可咀嚼零食；其中必须考虑制剂赋形剂的生理相容性。特别优选的施用形式是片剂、胶囊剂、食品添加剂或可咀嚼零食。
本发明式(I)化合物以未经修饰的形式或者优选地与制剂领域常用的助剂一起应用，因此可以以已知方式进行加工以得到例如可乳化浓缩物、可直接稀释的溶液、稀释乳液、可溶性粉剂、粉末混合物、颗粒或在聚合物质中的微囊。关于组合物，按照预期目标和当前环境来选择应用方法。
制剂，即活性剂、制备物或组合物，其含有一种或多种活性成分以及任选的固体或液体辅助剂，以本身已知的方式生产，例如通过将活性成分与辅助剂例如与溶剂、固体载体和/或表面活性化合物(表面活性剂)紧密混合和/或研磨。
所述溶剂可以是：醇，例如乙醇、丙醇或丁醇以及二元醇及其醚和酯如丙二醇、二丙二醇醚、乙二醇、乙二醇一甲醚或一乙醚；酮，例如环己酮、异佛尔酮或diacetanolalcohol，强极性溶剂，例如N-甲基-2-吡咯烷酮、二甲基亚砜或二甲基甲酰胺或水、植物油，例如菜油、蓖麻油、椰子油或大豆油以及如果适宜的话还有硅油。
适当的表面活性剂是例如非离子型表面活性剂例如壬基苯酚聚乙氧基乙醇；蓖麻油聚乙二醇醚例如聚乙二醇甘油羟基硬脂酸酯40；聚乙二醇；聚氧化丙烯/聚氧化乙烯加合物；或者聚氧化乙烯脱水山梨糖醇的脂肪酸酯例如聚氧化乙烯脱水山梨糖醇单油酸酯。
例如用于片剂和大丸剂的固体载体可以是经过化学修饰的可溶于水或醇的聚合天然物质如淀粉、纤维素或蛋白质衍生物(例如甲基纤维素、羧甲基纤维素、乙基羟乙基纤维素、蛋白质如玉米蛋白、明胶等)以及合成聚合物如聚乙烯醇、聚乙烯吡咯烷酮等。片剂还含有填充剂(例如淀粉、微晶纤维素、糖、乳糖等)、助流剂和崩解剂。
如果驱虫剂以饲料浓缩物的形式存在，则所用载体例如有功能饲料(performancefeeds)、饲料谷物或蛋白质浓缩物。这类饲料浓缩物或组合物除了活性成分以外还可以含有添加剂、维生素、抗生素、化疗剂或其它杀虫剂、主要是抑菌剂(bacteriostats)、抑真菌剂、抗球虫剂或者甚至激素制备物、具有同化作用的物质或促进生长的物质(其影响屠宰动物的肉的质量或者以其它方式有益于生物体)。
式(I)化合物的适当组合物还可包含其他添加剂，例如稳定剂、抗氧化剂如生育酚类诸如α-生育酚，消泡剂、粘度调节剂、粘合剂、颜料或增粘剂，以及其他活性成分，以便获得特定效果。优选地，组合物包含0.001-1％w/v的一种或多种抗氧化剂。如果需要，本发明的制剂可含有颜料，例如以0.001-1％w/v的量。
通常，根据本发明的驱虫组合物含有0.1-99重量％尤其是0.1-95重量％的式(I)化合物，99.9-1重量％尤其是99.8-5重量％的固体或液体混合物，包括0-25重量％尤其是0.1-25重量％的表面活性剂。
在用于害虫控制的各本发明的方法中或者在各种本发明的害虫控制组合物中，式(I)化合物可以以它们的所有空间构型或其混合物使用。
本发明还包括预防性地保护温血动物、尤其是生产性家畜和宠物特别是狗和猫免受寄生性蠕虫损害的方法，其特征在于，将式(I)化合物或由其制备的活性成分制剂作为饲料或饮水的添加剂或者也可以以固体或液体形式经口或通过注射或胃肠道外施用于温血动物。本发明还包括用于所述方法之一的本发明的式(I)化合物。
根据本发明的式(I)化合物可以单独使用或者与其他杀微生物剂组合使用。可将其与具有相同活性范围的杀虫剂组合，例如以提高活性或者将其与具有其他活性范围的物质组合，例如以拓宽活性范围。其还可对加入所谓的驱虫剂是敏感的。
下列实施例进一步阐明了本发明。
在各种情况下，利用下述方法B，使用装配反相柱的Waters Autopurification(HPLC/MS)系统进行纯化的样品的分析。将样品通过m/z和保留时间表征。在各情况下，上文给出的保留时间与所用溶剂系统相关，所述溶剂系统包含两种不同溶剂，溶剂A：H2O+0.01％HCOOH和溶剂B：CH3CN+0.01％HCOOH)。
-方法B：柱子Waters XTerra MS C185μm，50X4.6mm(Waters)，流速
3.00mL/min，具有表中给出的时间依赖的梯度：
时间[min] A[％] B[％]
0 90 10
0.5 90 10
2.5 5 95
2.8 5 95
2.9 90 10
3.0 90 10
实施例1A
2-(甲基磺酰氨基)-5-吗啉代-N-(3,4,5-三氯苯基)苯甲酰胺的合成(表1中的Ex.1.2)
步骤A：5-氯-2-硝基-N-(3,4,5-三氯苯基)苯甲酰胺.
将5-氯-2-硝基苯甲酸(10g)用亚硫酰氯(7.2mL)回流处理4h。真空除去过量的SOCl2。将CH2Cl2(100mL)加入到酰氯中。在0℃，缓慢加入在100mL CH2Cl2中的3,4,5-三氯苯胺(9.7g)和NEt3(13.8mL)。将反应混合物升温，并将其在rt(室温)搅拌过夜。将反应混合物用200mL乙醚稀释。加入10mL HCl 2N和200mL H2O，并搅拌混合物，直到形成黄色沉淀。将沉淀物滤出，并在分析前，高真空干燥(产率：66％)。LCMS(方法B)：380.59(M+H)+，1.97min。
步骤B:5-吗啉代-2-硝基-N-(3,4,5-三氯苯基)苯甲酰胺
向300mg 5-氯-2-硝基-N-(3,4,5-三氯苯基)苯甲酰胺的1.5mL DMF溶液中，加入吗啉(206μL)。将反应混合物在110℃加热1.5h。处理后，用AcOEt萃取，将混合物蒸发至干。标题混合物是足够纯的，可用于步骤B中(产率：71％)。LCMS(方法B)：427.7(M-H)-，位于1.81min。
步骤C：2-氨基-5-吗啉代-N-(3,4,5-三氯苯基)苯甲酰胺
在N2气下，将5-吗啉代-2-硝基-N-(3,4,5-三氯苯基)苯甲酰胺(230mg)的4mLEtOH/H2O(3/1)溶液用Fe(208mg)和HCl 25％(4μL)处理，并将反应混合物在rt下搅拌4h。当完成还原时，将反应混合物在硅藻土垫上过滤，并用乙酸乙酯冲洗。真空蒸发滤液。加入乙酸乙酯，并将有机层用盐水冲洗，用MgSO4干燥，并蒸发至干(产率：95％)。LCMS(方法B)：399.68(M+H)+，位于1.61min。
步骤D：2-(甲基磺酰氨基)-5-吗啉代-N-(3,4,5-三氯苯基)苯甲酰胺
加入N2脱气的2-氨基-5-吗啉代-N-(3,4,5-三氯苯基)苯甲酰胺(193mg)的3mLCH2Cl2溶液、吡啶(0.194mL)。将混合物冷却至0℃后，然后滴加甲烷磺酰氯(0.037mL)。将反应混合物在rt下搅拌过夜，然后用50mL乙酸乙酯稀释。将有机层用饱和Na2CO3溶液洗涤，用盐水洗涤，然后经MgSO4干燥，并蒸发至干(产率：43％)。LCMS(方法B)：477.7(M+H)+，位于1.78min。
实施例1B
N-(3,5-双(三氟甲基)苯基)-5-(2-氟吡啶-3-基)-2-(甲基磺酰氨基)苯甲酰胺(表1中的Ex.1.14)
步骤A：5-溴-2-(甲基磺酰氨基)苯甲酸甲酯
将N2脱气的2-氨基-5-溴苯甲酸甲酯(2.8g)的10mL吡啶溶液冷却至0℃后，滴加甲烷磺酰氯(0.9mL)。将反应混合物在rt搅拌过夜，然后用50mL乙酸乙酯稀释。将有机层用饱和Na2CO3溶液洗涤，用盐水洗涤，然后经MgSO4干燥，并蒸发至干(产率：82％)。LCMS(方法B)：305.6(M-H)-，位于1.55min。
步骤B：5-溴-2-(甲基磺酰氨基)苯甲酸
将5-溴-2-(甲基磺酰氨基)苯甲酸甲酯(3.15g)悬浮于THF(20mL,1/1)中。加入NaOH 4N(6.9mL)，并将反应混合物回流搅拌4h。一旦完成，将反应混合物用2N HCl(1mL)处理，并用乙酸乙酯萃取两次。将合并的有机层用H2O、盐水洗涤，经Na2SO4干燥，过滤并蒸发至干。经LCMS，标题产物是足够纯的，以至于不需要进一步纯化而用于下一步骤。(产率：66％)
LCMS(方法B)：291.64(M-H)-，位于1.2min。
步骤C:N-(3,5-双(三氟甲基)苯基)-5-溴-2-(甲基磺酰氨基)苯甲酰胺.
将5-溴-2-(甲基磺酰氨基)苯甲酸(2.4g)用亚硫酰氯(23mL)回流处理4h。真空除去过量的SOCl2。将CH2Cl2(20mL)加入到酰氯中。在0℃，缓慢加入3,5-双(三氟甲基)苯胺(1.4mL)和NEt3(5.68mL)的10mL CH2Cl2溶液。将反应混合物温热，并将其在rt搅拌过夜。
将反应混合物用30mL CH2Cl2稀释。加入20mL HCl 2N和20mL H2O，并搅拌混合物，直到形成黄色沉淀。将沉淀物滤出，并在分析前高真空干燥(产率：67％)。
LCMS(方法B)：502.93(M-H)-，位于1.99min。
步骤D：N-(3,5-双(三氟甲基)苯基)-5-(2-氟吡啶-3-基)-2-(甲基磺酰氨基)苯甲酰胺
在N2下，向N-(3,5-双(三氟甲基)苯基)-5-溴-2-(甲基磺酰氨基)苯甲酰胺(0.2g)和2-氟-3-(4,4,5,5-四甲基-1,3,2-二氧硼杂环戊-2-基)吡啶(133mg)的二噁烷/H2O(6mL,1/1)溶液中，加入Na2CO3(252mg)，Pd(dppf)Cl2.CH2Cl2(355mg)。将反应混合物在80℃下搅拌3h。用乙酸乙酯稀释，经硅藻土过滤。将滤液用H2O、盐水洗涤，经Na2SO4干燥，过滤并蒸发至干。
将粗混合物经快速色谱纯化，用梯度的100％庚烷至60％庚烷/40％乙酸乙酯洗脱，得到标题化合物，产率25％。
LCMS(方法C)：521.8(M+H)+，位于1.90min。
用类似于上述的方法，制备下表1中提到的物质。化合物是下式：
其中，A和(R)r的含义是表1中给出的。
根据上述HPLC/MS表征方法(方法B)，得到下述物理数据。Rt指“保留时间”。
表1：
实施例2
5-苯氧基-2-(苯基磺酰氨基)-N-(3,4,5-三氯苯基)苯甲酰胺(表2中的Ex.2.2)
步骤A：2-硝基-5-苯氧基-N-(3,4,5-三氯苯基)苯甲酰胺.
将5-氯-2-硝基-N-(3,4,5-三氯苯基)苯甲酰胺(29.1g)、K2CO3(21.3g)和苯酚(8g)的DMA溶液在140℃下加热14h。将反应混合物倒入H2O(100mL)中，滤出沉淀物，高真空干燥，得到棕色固体(产率：80％)。LCMS(方法B):436.6(M-H)-，位于2.14min.
步骤B：2-氨基-5-苯氧基-N-(3,4,5-三氯苯基)苯甲酰胺
用类似于实施例1中步骤C所述的方式，将2-硝基-5-苯氧基-N-(3,4,5-三氯苯基)苯甲酰胺用铁处理(产率：27％)。LCMS(方法B)：406.7(M+H)+，位于2.28min。
步骤C：5-(4-氯苯氧基)-2-(甲基磺酰氨基)-N-(3,4,5-三氯苯基)苯甲酰胺
向N2脱气的2-氨基-5-苯氧基-N-(3,4,5-三氯苯基)苯甲酰胺(0.26mg)的2mLCH2Cl2溶液中，加入吡啶(0.25mL)。将混合物冷却至0℃后，滴加苯磺酰氯(0.124mg)。将反应混合物在rt搅拌过夜，然后用另外的5mL CH2Cl2稀释。将有机层用饱和Na2CO3溶液、盐水洗涤，然后经MgSO4干燥，并蒸发至干(产率：81％)。LCMS(方法B)：546.7(M+H)+，位于2.39min。
用类似于上述的方法，制备下表2中提到的物质。化合物具有下式：
其中，(R1)r、(R)m和X的含义是表2中给出的。
根据上述HPLC/MS表征方法(方法B)，得到下述物理数据。
表2：
实施例3
2-(甲基磺酰氨基)-N-(3,4,5-三氯苯基)-5-((2-(三氟甲基)吡啶-3-基)氧基)苯甲酰胺(表3中的Ex 3.2)
步骤A：2-硝基-5-((2-(三氟甲基)吡啶-3-基)氧基)苯甲酸甲酯.
用类似于实施例3合成步骤A的方式，处理5-氯-2-硝基苯甲酸甲酯(产率：28％)。LCMS(方法B)：342.86(M+H)+，位于1.63min。
步骤B：2-硝基-5-((2-(三氟甲基)吡啶-3-基)氧基)苯甲酸.
在rt下，将2-硝基-5-((2-(三氟甲基)吡啶-3-基)氧基)苯甲酸甲酯(277mg)用NaOH 1N(4.13mL)的THF/MeOH(8mL,2/1)处理过夜(产率：98％)。LCMS(方法B)：328.84(M+H)+，位于1.33min。
步骤C：2-硝基-N-(3,4,5-三氯苯基)-5-((2-(三氟甲基)吡啶-3-基)氧基)苯甲酰胺
用类似于实施例1合成步骤A的方式，处理2-硝基-5-((2-(三氟甲基)吡啶-3-基)氧基)苯甲酸(产率：45％)。LCMS(方法B)：505.7(M+H)+，位于2.05min。
步骤D：2-氨基-N-(3,4,5-三氯苯基)-5-((2-(三氟甲基)吡啶-3-基)氧基)苯甲酰胺
用类似于实施例1步骤C的方式，处理2-硝基-N-(3,4,5-三氯苯基)-5-((2-(三氟甲基)吡啶-3-基)氧基)苯甲酰胺(产率：100％)。LCMS(方法B)：475.52(M+H)+，位于2.21min。
步骤E：2-(甲基磺酰氨基)-N-(3,4,5-三氯苯基)-5-((2-(三氟甲基)吡啶-3-基)氧基)苯甲酰胺
用类似于实施例1合成步骤D的方式，处理2-氨基-N-(3,4,5-三氯苯基)-5-((2-(三氟甲基)吡啶-3-基)氧基)苯甲酰胺(产率：20％)。LCMS(方法C)：553.7(M+H)+，位于2.07min。
用类似于上述的方法，制备下表3中提到的物质。化合物具有下式：
其中，A1的含义是表3中给出的。据上述HPLC/MS表征方法，得到下述物理数据。
表3：
实施例4
5-(4-氯苯氧基)-2-(甲基磺酰氨基)-N-(4-(三氟甲基)唑-2-基)苯甲酰胺
(表4中的Ex 4.16)
步骤A：5-(4-氯苯氧基)-2-硝基苯甲酸甲酯
用类似于实施例3合成步骤A的方式，处理5-氯-2-硝基苯甲酸甲酯(产率：90％)。LCMS(方法B)：305.0(M+H)+，位于1.67min。
步骤B：2-氨基-5-(4-氯苯氧基)苯甲酸甲酯
用类似于实施例1步骤C的方式，处理5-(4-氯苯氧基)-2-硝基苯甲酸甲酯(产率：100％)。LCMS(方法B)：277.82(M+H)+，位于1.88min。
步骤C：5-(4-氯苯氧基)-2-(甲基磺酰氨基)苯甲酸甲酯
用类似于实施例1合成步骤D的方式，处理2-氨基-5-(4-氯苯氧基)苯甲酸甲酯(产率：95％)。LCMS(方法B)：353.78(M-H)-，位于1.84min。
步骤D：5-(4-氯苯氧基)-2-(甲基磺酰氨基)苯甲酸
用类似于实施例4合成步骤B的方式，皂化5-(4-氯苯氧基)-2-(甲基磺酰氨基)苯甲酸甲酯(产率：96％)。LCMS(方法B)：339.62(M-H)-，位于1.61min。
步骤E：5-(4-氯苯氧基)-2-(甲基磺酰氨基)-N-(4-(三氟甲基)唑-2-基)苯甲酰胺
用类似于实施例1合成步骤A的方式，处理5-(4-氯苯氧基)-2-(甲基磺酰氨基)苯甲酸(产率：3％)。LCMS(方法B)：475.64(M+H)+，位于1.70min。
用类似于上述的方法，制备下表4中提到的物质。化合物具有下式：
其中，Y和R0的含义是表4中给出的。根据上述HPLC/MS表征方法(方法B)，得到下述物理数据。
表4：
生物学实施例：
胃肠道幼虫发育测定
将新鲜收集和净化的线虫卵用于接种含有待评价抗寄生虫活性的测试物质的适宜布局的孔板以及允许卵完全发育成第三龄幼虫的培养基。将板于25℃和60％相对湿度温育6天。记录卵孵化和随即发生的幼虫发育，以鉴定可能的杀线虫活性。效力表示为减少的卵孵化、减少的L3发育或任何阶段幼虫的停顿&死亡的百分比。在10ppm，化合物编号1.4、1.10-1.12、1.14、1.16-1.21、1.23、1.25-1.26、1.29-1.33、2.1、2.22、2.28、2.42-2.43、3.1-3.2、4.1、4.3-4.8、4.19-4.24、4.28、4.32、4.34、4.36-4.37、4.39、4.42-4.43和4.51达到≥60％效力，并由此认为是有活性的。
犬恶丝虫(Dirofilaria immitis)微丝蚴测定
从供体动物狗的血液，制备新鲜收集和净化的犬恶丝虫微丝蚴。然后将微丝蚴分配在含有待评价抗寄生虫活性的测试物质的布局的微孔板。将板于25℃和60％相对湿度(RH)温育48小时。然后，记录微丝蚴的能动性，以测定效力。将效力表示为与对照和标准相比能动性减少的百分数。在10ppm，化合物编号1.2-1.4和1.6-1.33、2.1-2.20、2.22-2.44、2.46、3.1-3.4、4.1-4.10、4.12-4.16、4.17-4.18、4.21-4.29、4.31-4.39、4.42和4.46-4.52显示大于50％的效力，并由此认为是有活性的。
沙鼠中的魏氏棘唇丝虫(Acanthocheilonema viteae)
通过皮下注射，使沙鼠人工感染80L3幼虫。感染后第5天至第9天，用配制的测试化合物经管饲法进行连续处理。感染后84天，将沙鼠放血，利用Fuchs-Rosenthal计数室和显微镜，用于计数循环微丝蚴。仅将具有比安慰剂治疗组至少低50％的平均循环微丝蚴的测试组完全解剖，以回收成年蠕虫。利用Abbot公式，将效力表示为与安慰剂治疗组相比蠕虫数的％减少。在10mg/kg，化合物编号1.6-1.8、1.17、1.25、1.30、1.32、2.24、4.13、4.24显示80％以上的效力。
成年肝吸虫-体外测试
将从牛或绵羊肝新鲜采集的成年肝片形吸虫(Fasciola hepatica)分布在含有4mL RPMI完全培养基的12-孔板上(每孔1条吸虫)，并在37℃孵卵器中保持约12小时。除去培养基后，通过个体吸虫移动的视频-记录，测定吸虫的存活力(预置值)。以100μg/mL的浓度，加入测试化合物，并在6和24小时后，测量吸虫的移动。将效力表示为基于预置值和未治疗的对照的移动减少的百分数。在所述测试中，下述实施例在6h后显示超过>90％效力，并在24h后显示>95％效力，被认为阳性的：2.2，4.13。

Claims (11)

1.式(I)化合物或其盐或对映异构体，
其中
n是0或1；
A是C1-C6-烷基；C1-C6-卤代烷基；C3-C6-环烷基；C3-C6-卤代环烷基；含有选自B、N、O和S的1-3个相同或不同杂原子的5-或6-元杂环烷基，其是未取代的或进一步被卤素、C1-C4-烷基或C1-C4-烷氧基取代；或者是苯基，其是未取代的或被下列基团取代：卤素、C1-C6-烷基、C1-C6-卤代烷基、C3-C6-环烷基、C3-C6-卤代环烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C1-C6-烷硫基、C1-C6-卤代烷硫基、C1-C6-烷基-亚磺酰基、C1-C6-卤代烷基亚磺酰基、C1-C6-烷基磺酰基、C1-C6-卤代烷基磺酰基、SF5、氨基、N-单-或N,N-二-C1-C6-烷基氨基、三-C1-C4-烷基硅烷基、C1-C6-烷氧基羰基、氨基羰基、N-单-或N,N-二-C1-C6-烷基氨基羰基、氨基磺酰基、N-单-或N,N-二-C1-C6-烷基氨基磺酰基、C1-C6-烷氧基羰基氨基、N-C1-C4-烷基-N-C1-C6-烷氧基羰基氨基、氰基、硝基、或者未取代的或卤素-、C1-C4-烷基-、C1-C4-卤代烷基-、C1-C4-烷氧基-、C1-C4-卤代烷氧基-、氨基-、氰基-或硝基-取代的C3-C6-杂环基；或者是肉桂基，其苯基基团是未取代的或被卤素、C1-C4-烷基或C1-C4-烷氧基取代的；或者是杂芳基，其是未取代的或者被下列基团取代：卤素、氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C2-C4-烷酰基、5-或6-元杂环烷基-C1-C2-烷基或者未取代或卤素-、C1-C4-烷基-或C1-C4-烷氧基-取代的苯基；或者是含有总计8-10个环成员的杂二环基团，其中1-5个成员是选自B、N、O和S的相同或不同杂原子，并且其中0-2个成员是基团–C(O)-，该二环基团是未取代的或被卤素、氰基、羟基、C1-C4-烷基或C1-C4-卤代烷基取代的；
R2是H或–S(O2)-T；
T是C1-C6-烷基，其是未取代的或被卤素、三甲基硅烷基、C3-C6-环烷基、羧基或C1-C4-烷氧基羰基取代；C3-C6-环烷基；C6-C12-二碳环基；苯基，其是未取代的或被卤素、氰基、硝基、C1-C4-烷基、C1-C4-卤代烷基或C1-C4-烷氧基取代的；5-或6元杂芳基，其是未取代的或被卤素、氰基、硝基、C1-C4-烷基、C1-C4-卤代烷基或C1-C4-烷氧基取代的；含有选自N、O、S和S(O2)的1-3个相同或不同杂原子的5-或6-元杂环烷基，其是未取代的或被C1-C4-烷基、C1-C2-烷氧基羰基或苄氧基羰基取代的；基团氨基；或N-单-或N,N-二-C1-C4-烷基氨基；
R3是C1-C4-烷基、未取代的或卤素-、C1-C4-烷基-或C1-C4-卤代烷基-取代的苯基、未取代的或卤素-、C1-C4-烷基-或C1-C4-卤代烷基-取代的吡啶基、C1-C4-烷氧基羰基甲基或吗啉-4-基-羰基甲基；
R0是H或羟基；且
Y是
(i)苯基或苯基氨基，其是被选自以下的一个或多个相同或不同基团取代的：卤素；C1-C6-烷基；C1-C6-卤代烷基；C3-C6-环烷基；C3-C6-卤代环烷基；羟基；C1-C6-烷氧基；C1-C6-卤代烷氧基；C1-C6-烷硫基；C1-C6-卤代烷硫基；C1-C6-烷基-亚磺酰基；C1-C6-卤代烷基亚磺酰基；C1-C6-烷基磺酰基；C1-C6-卤代烷基磺酰基；SF5；氨基；N-单-或N,N-二-C1-C6-烷基氨基；三-C1-C4-烷基硅烷基；C1-C6-烷氧基羰基；氨基羰基；N-单-或N,N-二-C1-C6-烷基氨基羰基；氨基磺酰基；N-单-或N,N-二-C1-C6-烷基氨基磺酰基；N-C1-C6-烷基磺酰基氨基；C1-C6-烷氧基羰基氨基；N-C1-C4-烷基-N-C1-C6-烷氧基羰基氨基；氰基；硝基；和未取代的或卤素-、C1-C4-烷基-、C1-C4-卤代烷基-、C1-C4-烷氧基-、C1-C4-卤代烷氧基-、氨基-、氰基-或硝基-取代的C3-C6-杂环基；或者是
(ii)5-或6元杂芳基或杂芳基氨基，其各自是未取代的或被以下基团取代：卤素、氰基、硝基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-烷氧基羰基、C2-C4-烷酰基、或者苯基或苯磺酰基，其各自是未取代的或被卤素、氰基、硝基、甲基或甲氧基取代的；或者是
(iii)苯甲酰基或者5-或6元杂芳基羰基，其各自是未取代的或者被卤素、氰基、硝基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-烷氧基羰基、C2-C4-烷酰基或苯基取代的；或者是
(iv)C6-C12-二碳环基团；或者是
(v)含有总计8-10个环成员的杂二环基团，其中1-5优选1-2个成员是选自B、N、O和S的相同或不同杂原子，并且其中0-2个成员是基团–C(O)-，该二环基团是未取代的或被卤素、氰基、羟基、C1-C4-烷氧基、C1-C4-烷基或C1-C4-卤代烷基取代的；或者是
(vi)基团–H2C-C(O)-NH-R4，其中R4是C1-C4-卤代烷基、C2-C3-炔基或者氰基-C1-C4-烷基；或者
R0和Y与它们连接的N-原子一起形成哌啶基或哌嗪基基团，其被下述基团取代：C1-C4-烷基、C1-C4-烷氧基、未取代或卤素-、C1-C4-烷基-、C1-C4-卤代烷基-、氨基-和/或C1-C4-烷氧基-取代的苯基或苯甲酰氨基、或者未取代或C1-C4-烷基-、C1-C4-卤代烷基-、C3-C6-环烷基-或卤素-取代的吡啶基或嘧啶基；前提是：
(i)如果T是CH3，则A和Y中的至少一个一定不是苯基基团；和
(ii)如果A是C1-C6-烷基或C1-C6-卤代烷基，则T是未取代或如上述取代的C1-C6-烷基。
2.式(Ia)的根据权利要求1所述的化合物
其中Y’是苯基，其被选自以下的一个或多个相同或不同基团取代：卤素；C1-C6-烷基；C1-C6-卤代烷基；C3-C6-环烷基；C3-C6-卤代环烷基；羟基；C1-C6-烷氧基；C1-C6-卤代烷氧基；C1-C6-烷硫基；C1-C6-卤代烷硫基；C1-C6-烷基-亚磺酰基；C1-C6-卤代烷基亚磺酰基；C1-C6-烷基磺酰基；C1-C6-卤代烷基磺酰基；SF5；氨基；N-单-或N,N-二-C1-C6-烷基氨基；三-C1-C4-烷基硅烷基；C1-C6-烷氧基羰基；氨基羰基；N-单-或N,N-二-C1-C6-烷基氨基羰基；氨基磺酰基；N-单-或N,N-二-C1-C6-烷基氨基磺酰基；N-C1-C6-烷基磺酰基氨基；C1-C6-烷氧基羰基氨基；N-C1-C4-烷基-N-C1-C6-烷氧基羰基氨基；氰基；硝基；和未取代或卤素-、C1-C4-烷基-、C1-C4-卤代烷基-、C1-C4-烷氧基-、C1-C4-卤代烷氧基-、氨基-、氰基-或硝基-取代的C3-C6-杂环基；且
A’是C1-C6-烷基；C1-C6-卤代烷基；C3-C6-环烷基；C3-C6-卤代环烷基；含有选自B、N、O和S的1-3个相同或不同杂原子的5-或6-元杂环烷基，其是未取代的或进一步被卤素、C1-C4-烷基或C1-C4-烷氧基取代的；杂芳基，其是未取代的或进一步被下述基团取代：卤素、氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C1-C4-烷酰基、5-或6-元杂环烷基-C1-C2-烷基或者未取代的或卤素-、C1-C4-烷基-或C1-C4-烷氧基-取代的苯基；或者是含有总计8-10个环成员的杂二环基团，其中1-5个优选1或2个成员是选自B、N、O和S的相同或不同杂原子，并且其中0-2个成员是基团–C(O)-，该二环基团是未取代的或被卤素、氰基、羟基、C1-C4-烷基或C1-C4-卤代烷基取代的。
3.根据权利要求2所述的化合物，其中Y’是苯基，其被选自卤素或CF3的2个或3个相同或不同基团取代；并且A’是C1-C4-烷基；CF3；吡咯烷基、哌嗪基、吗啉基或二氧硼杂环戊烷基，其各自是未取代的或被甲基取代的；吡咯基、吡唑基、三唑基、噻吩基、噻嗪基、噻唑基、吡啶基或嘧啶基，其各自是未取代的或被卤素、氰基、C1-C2-烷基、C1-C2-烷氧基、C1-C2-卤代烷基、乙酰基、丙酰基、苯基或吗啉-4-基-甲基取代的；或者吲哚基、苯并吡唑基或苯并噻唑基，其各自是未取代的或被甲基取代的；并且n是1。
4.式(Ib)的根据权利要求1所述的化合物
其中A是苯基，其是未取代的或被以下基团取代：卤素、C1-C6-烷基、C1-C6-卤代烷基、C3-C6-环烷基、C3-C6-卤代环烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C1-C6-烷硫基、C1-C6-卤代烷硫基、C1-C6-烷基-亚磺酰基、C1-C6-卤代烷基亚磺酰基、C1-C6-烷基磺酰基、C1-C6-卤代烷基磺酰基、SF5、氨基、N-单-或N,N-二-C1-C6-烷基氨基、三-C1-C4-烷基硅烷基、C1-C6-烷氧基羰基、氨基羰基、N-单-或N,N-二-C1-C6-烷基氨基羰基、氨基磺酰基、N-单-或N,N-二-C1-C6-烷基氨基磺酰基、C1-C6-烷氧基羰基氨基、N-C1-C4-烷基-N-C1-C6-烷氧基羰基氨基、氰基、硝基、或者未取代或卤素-、C1-C4-烷基-、C1-C4-卤代烷基-、C1-C4-烷氧基-、C1-C4-卤代烷氧基-、氨基-、氰基-或硝基-取代的C3-C6-杂环基；
Y是苯基，其被选自下述的一个或多个相同或不同基团取代：卤素；C1-C6-烷基；C1-C6-卤代烷基；C3-C6-环烷基；C3-C6-卤代环烷基；羟基；C1-C6-烷氧基；C1-C6-卤代烷氧基；C1-C6-烷硫基；C1-C6-卤代烷硫基；C1-C6-烷基-亚磺酰基；C1-C6-卤代烷基亚磺酰基；C1-C6-烷基磺酰基；C1-C6-卤代烷基磺酰基；SF5；氨基；N-单-或N,N-二-C1-C6-烷基氨基；三-C1-C4-烷基硅烷基；C1-C6-烷氧基羰基；氨基羰基；N-单-或N,N-二-C1-C6-烷基氨基羰基；氨基磺酰基；N-单-或N,N-二-C1-C6-烷基氨基磺酰基；N-C1-C6-烷基磺酰基氨基；C1-C6-烷氧基羰基氨基；N-C1-C4-烷基-N-C1-C6-烷氧基羰基氨基；氰基；硝基；和未取代或被卤素-、C1-C4-烷基-、C1-C4-卤代烷基-、C1-C4-烷氧基-、C1-C4-卤代烷氧基-、氨基-、氰基-或硝基-取代的C3-C6-杂环基；
T是C2-C6-烷基，其是未取代的或被卤素、三甲基硅烷基、C3-C6-环烷基、羧基或C1-C4-烷氧基羰基取代的；C3-C6-环烷基；C6-C12-二碳环基；苯基，其是未取代的或被卤素、氰基、硝基、C1-C4-烷基、C1-C4-卤代烷基或C1-C4-烷氧基取代的；5-或6元杂芳基，其是未取代的或进一步被卤素、C1-C4-烷基或C1-C4-烷氧基取代的；氨基；N-单-或N,N-二-C1-C4-烷基氨基；含有选自N、O、S和S(O2)的1-3个相同或不同杂原子的5-或6-元杂环烷基，其是未取代的或进一步被C1-C4-烷基取代的；或者基团且
R3是C1-C4-烷基、未取代或卤素-、C1-C4-烷基-或C1-C4-卤代烷基-取代的苯基、未取代或卤素-、C1-C4-烷基-或C1-C4-卤代烷基-取代的吡啶基、C1-C4-烷氧基羰基甲基或吗啉-4-基-羰基甲基。
5.根据权利要求4所述的化合物，其中A是苯基，其是未取代的或者被氯、氟或CF3单-取代的，Y是苯基，其是被选自卤素或CF3的2个或3个相同或不同基团取代的，并且T是C2-C4-烷基，其是未取代的或被卤素、环丙基、环己基、三甲基硅烷基、羧基或C1-C2-烷氧基羰基取代的；环丙基或环己基；基团(+)-或(-)-樟脑；苯基，其是未取代的或被氟、氯、甲基、甲氧基、CF3或硝基取代的；或者吡啶基、噻吩基或嘧啶基；哌啶基、哌嗪基、四氢吡喃基、吗啉基、硫代吗啉基或硫代吗啉-4-基-1,1-二氧化物，其各自是未取代的或被甲基或苄氧基羰基取代的。
6.式(Ic)的根据权利要求1所述的化合物
其中A是苯基，其是未取代的或如权利要求1所定义那样取代的；
R0是H或羟基；并且
Y”是
(i)5-或6元杂芳基或杂芳基氨基，其各自还是未取代的或被以下基团取代：卤素、氰基、硝基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-烷氧基羰基、C1-C4-烷酰基或者苯基或苯磺酰基，其各自是未取代的或被卤素、氰基、硝基甲基或甲氧基取代；或者是
(ii)苯甲酰基或者5-或6元杂芳基羰基，其各自是未取代的或被卤素、氰基、硝基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-烷氧基羰基、C1-C4-烷酰基或苯基取代的；或者是
(iii)C6-C12-二碳环基团；或者是
(iv)含有总计8-10个环成员的杂二环基团，其中1-5个优选1-2个是选自B、N、O和S的相同或不同杂原子，并且其中0-2个是基团–C(O)-，所述二环基团是未取代的或被卤素、氰基、羟基、C1-C4-烷氧基、C1-C4-烷基或C1-C4-卤代烷基取代的；或者是
(v)基团–H2C-C(O)-NH-R4，其中R4是C1-C4-卤代烷基、C2-C3-炔基或氰基-C1-C4-烷基；或者
R0和Y与它们连接的N-原子一起形成哌啶基或哌嗪基基团，其被下述基团取代：C1-C4-烷基、C1-C4-烷氧基、未取代或卤素-、C1-C4-烷基-、卤代-C1-C4-烷基-、氨基-和/或C1-C4-烷氧基-取代的苯基或苯甲酰氨基、或者未取代或C1-C4-烷基-、C1-C4-卤代烷基-、C3-C6-环烷基-或卤素-取代的吡啶基或嘧啶基。
7.根据权利要求6所述的化合物，其中
A是苯基，其是未取代的或者被氯、氟或CF3单-取代的；
R0是H，且
Y”是
(i)2-、3-或4-吡啶基，其是未取代的或者被卤素、C1-C4-烷基或C1-C2-烷氧基取代的；2-噻吩基，其是未取代的或者被C1-C2-烷基、C1-C2-烷氧基羰基取代的；2-噻唑基，它是未取代的或者被下述基团取代：卤素、氰基、硝基、C1-C2-烷基、C1-C2-卤代烷基、C1-C2-烷氧基羰基、或苯基或苯磺酰基，其各自是未取代的或被卤素、氰基、硝基或甲基取代的；5-异噻唑基，其是未取代的或者被卤素或甲基取代的；2-噁唑基，其是未取代的或者被C1-C2-烷基或C1-C2-卤代烷基取代的；或者1,3,4-噻二唑-5-基，其是未取代的或者被C1-C2-烷基或C1-C2-卤代烷基取代的；2-、3-或4-吡啶基氨基，其是未取代的或被卤素、C1-C4-烷基或C1-C2-烷氧基取代的；或者
(ii)苯甲酰基，其是未取代的或者被卤素取代的，或者2-、3-或4-吡啶基羰基，其是未取代的或者被卤素或C1-C4-烷基取代的；或者
(iii)基团基团或茚满基；或者
(iv)苯并噻唑基、吲哚基、喹啉基、亚甲二氧苯基、苯并氧硼杂环戊基、三唑并嘧啶酮基或邻苯二甲酰肼基，其各自是未取代的或者被卤素、C1-C4-烷基、C1-C2-卤代烷基或羟基取代的；或者
(v)基团–H2C-C(O)-NH-CH2-C≡CH、–H2C-C(O)-NH-CH2-CN或–H2C-C(O)-NH-CH2-CF3；
或者R0和Y与其连接的N-原子一起形成哌啶基或哌嗪基基团，其被下述基团取代：甲基；甲氧基；卤素-、氨基-、甲氧基-或三氟甲基-取代的苯基或苯甲酰氨基；或者卤素-、三氟甲基-和/或环丙基-取代的吡啶基或嘧啶基。
8.用于控制寄生虫的组合物，除了载体和/或分散剂之外，其含有作为活性成分的根据权利要求1-7中任何一项所述的至少一种式(I)、(Ia)、(Ib)或(Ic)化合物。
9.根据权利要求1-7中任何一项所述的式(I)、(Ia)、(Ib)或(Ic)化合物，其用于控制温血动物内或温血动物上的体内寄生虫。
10.控制温血动物上的体内寄生虫的方法，其包含将兽医学有效量的根据权利要求1-7中任何一项所述的至少一种式(I)、(Ia)、(Ib)或(Ic)化合物施用至温血动物。
11.根据权利要求1-7中任何一项所述的式(I)、(Ia)、(Ib)或(Ic)化合物在制备对抗温血动物内或温血动物上的体内寄生虫的兽用组合物或药物组合物中的用途。
CN201580046065.2A 2014-08-29 2015-08-27 作为抗蠕虫药的新的磺酰基氨基苯甲酰胺化合物 Active CN106660961B (zh)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP14182960.6 2014-08-29
EP14182960.6A EP2990403A1 (en) 2014-08-29 2014-08-29 Anthranilamides, sulfonamides and nitro analogues derived therefrom as anthelmintics
PCT/US2015/047214 WO2016033341A1 (en) 2014-08-29 2015-08-27 Novel sulfonylaminobenzamide compounds as anthelmintics

Publications (2)

Publication Number Publication Date
CN106660961A true CN106660961A (zh) 2017-05-10
CN106660961B CN106660961B (zh) 2020-05-05

Family

ID=51454570

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201580046065.2A Active CN106660961B (zh) 2014-08-29 2015-08-27 作为抗蠕虫药的新的磺酰基氨基苯甲酰胺化合物

Country Status (14)

Country Link
US (2) US10047040B2 (zh)
EP (3) EP2990403A1 (zh)
JP (1) JP6385560B2 (zh)
KR (3) KR102341812B1 (zh)
CN (1) CN106660961B (zh)
AU (2) AU2015308828B2 (zh)
BR (2) BR122020010663B1 (zh)
CA (2) CA2956512C (zh)
DK (2) DK3792251T3 (zh)
EA (1) EA032822B1 (zh)
ES (2) ES2865121T3 (zh)
MX (2) MX2020013849A (zh)
NZ (1) NZ728623A (zh)
WO (1) WO2016033341A1 (zh)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2990403A1 (en) * 2014-08-29 2016-03-02 Novartis Tiergesundheit AG Anthranilamides, sulfonamides and nitro analogues derived therefrom as anthelmintics
EP3508475A4 (en) 2016-08-30 2020-04-15 Nippon Soda Co., Ltd. SULFONYLAMINOBENZAMIDE COMPOUND AND PEST CONTROL
JPWO2019167863A1 (ja) * 2018-02-27 2021-03-04 日本曹達株式会社 ヘテロアリールスルホンアミド化合物および有害生物防除剤
HUE064831T2 (hu) * 2018-05-22 2024-04-28 Orsobio Inc Szulfonil-amino-benzamid származékok
TWI748194B (zh) 2018-06-28 2021-12-01 德商菲尼克斯 Ｆｘｒ有限責任公司 含有雙環核心部分之新穎lxr調節劑

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU5948286A (en) * 1985-07-03 1987-01-08 Hoechst A.G. Anthranilic acid derivatives
SU1685935A1 (ru) * 1989-12-21 1991-10-23 Институт медицинской паразитологии и тропической медицины им.Е.И.Марциновского 2-[(Бензо-2,1,3-тиадиазол-4-сульфонил)амино] бензойные кислоты в качестве промежуточных продуктов в синтезе N-(4-хлорфенил)- или N-(3,4-дихлорфенил)-2-[(бензо-2,1,3-тиадиазол-4-сульфонил)амино]-5-хлорбензамида, обладающих антигельминтной активностью
SU1685937A1 (ru) * 1989-12-21 1991-10-23 Институт медицинской паразитологии и тропической медицины им.Е.И.Марциновского 2-[(7-Бромбензо-2,1,3-тиадиазол-4-сульфонил) амино]-5-хлорбензойна кислота в качестве промежуточного продукта в синтезе 2-[(7-бромбензо-2,1,3-тиадиапрозол-4-сульфонил) амино]-5-хлор-N-(4-хлорфенил) бензамида, обладающего антигельминтной активностью
US5077330A (en) * 1988-08-29 1991-12-31 Armstrong World Industries, Inc. Conductive polyurethane-urea/polyethylene oxide
US5081125A (en) * 1989-09-26 1992-01-14 Ciba-Geigy Corporation Anthelmintics
SU1754712A1 (ru) * 1989-12-21 1992-08-15 Институт медицинской паразитологии и тропической медицины им.Е.И.Марциновского N-(3-нитро-4-хлорфенилсульфонил)-антранилова кислота в качестве промежуточного продукта дл получени N-(4-хлорфенил)-2-[(3-нитро-4-хлорфенилсульфонил)-амино]-5-бромбензамида, обладающего противотрихоцефалезной активностью

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU6651581A (en) * 1980-02-01 1981-08-06 Rhone-Poulenc, Inc. 2-nitro-(substituted phenoxy) benzoyl derivatives as herbicides
CA1338238C (en) * 1988-01-07 1996-04-09 David John Carini Angiotensin ii receptor blocking imidazoles and combinations thereof with diuretics and nsaids
EP0420805A3 (en) * 1989-09-26 1991-10-16 Ciba-Geigy Ag Anthelmintic compounds
CN1332943C (zh) * 1998-07-08 2007-08-22 萨诺费－阿文蒂斯德国有限公司 硫取代的磺酰基氨基羧酸n－芳基酰胺,其制备方法、用途以及含有该化合物的药物制剂
AU5881000A (en) * 1999-06-24 2001-01-09 Smithkline Beecham Corporation Macrophage scavenger receptor antagonists
EP1427705A2 (en) * 2001-09-21 2004-06-16 E.I. Du Pont De Nemours And Company Insecticidal diamides
WO2005085188A2 (en) * 2004-03-02 2005-09-15 Compass Pharmaceuticals Llc Compounds and methods for anti-tumor therapy
BRPI0817483A2 (pt) * 2007-10-05 2016-07-26 Sanofi Aventis Deutschland uso de n-fenilamidas de ácido 2-sulfonilaminobenzoico substituídas por sulfonila no tratamento da dor
GB201402016D0 (en) * 2014-02-06 2014-03-26 Smiths Medical Int Ltd Ventilators and ventilator systems
EP2957557A1 (en) * 2014-06-17 2015-12-23 Novartis Tiergesundheit AG New compounds
MY187540A (en) 2014-08-01 2021-09-28 Nuevolution As Compounds active towards bromodomains
EP2990403A1 (en) * 2014-08-29 2016-03-02 Novartis Tiergesundheit AG Anthranilamides, sulfonamides and nitro analogues derived therefrom as anthelmintics

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU5948286A (en) * 1985-07-03 1987-01-08 Hoechst A.G. Anthranilic acid derivatives
US5077330A (en) * 1988-08-29 1991-12-31 Armstrong World Industries, Inc. Conductive polyurethane-urea/polyethylene oxide
US5081125A (en) * 1989-09-26 1992-01-14 Ciba-Geigy Corporation Anthelmintics
SU1685935A1 (ru) * 1989-12-21 1991-10-23 Институт медицинской паразитологии и тропической медицины им.Е.И.Марциновского 2-[(Бензо-2,1,3-тиадиазол-4-сульфонил)амино] бензойные кислоты в качестве промежуточных продуктов в синтезе N-(4-хлорфенил)- или N-(3,4-дихлорфенил)-2-[(бензо-2,1,3-тиадиазол-4-сульфонил)амино]-5-хлорбензамида, обладающих антигельминтной активностью
SU1685937A1 (ru) * 1989-12-21 1991-10-23 Институт медицинской паразитологии и тропической медицины им.Е.И.Марциновского 2-[(7-Бромбензо-2,1,3-тиадиазол-4-сульфонил) амино]-5-хлорбензойна кислота в качестве промежуточного продукта в синтезе 2-[(7-бромбензо-2,1,3-тиадиапрозол-4-сульфонил) амино]-5-хлор-N-(4-хлорфенил) бензамида, обладающего антигельминтной активностью
SU1754712A1 (ru) * 1989-12-21 1992-08-15 Институт медицинской паразитологии и тропической медицины им.Е.И.Марциновского N-(3-нитро-4-хлорфенилсульфонил)-антранилова кислота в качестве промежуточного продукта дл получени N-(4-хлорфенил)-2-[(3-нитро-4-хлорфенилсульфонил)-амино]-5-бромбензамида, обладающего противотрихоцефалезной активностью

Also Published As

Publication number Publication date
JP6385560B2 (ja) 2018-09-05
KR20180050434A (ko) 2018-05-14
EA201790191A1 (ru) 2017-07-31
KR20210157409A (ko) 2021-12-28
CA2956512C (en) 2020-08-04
CN106660961B (zh) 2020-05-05
US20180319741A1 (en) 2018-11-08
NZ728623A (en) 2018-07-27
DK3792251T3 (da) 2024-05-21
ES2981433T3 (es) 2024-10-08
MX2017002689A (es) 2017-12-12
AU2018204015B2 (en) 2020-03-05
MX2020013849A (es) 2022-09-21
BR122020010663B1 (pt) 2023-03-07
KR102341812B1 (ko) 2021-12-21
AU2015308828A1 (en) 2017-02-09
BR112017002750B1 (pt) 2023-05-02
EA032822B1 (ru) 2019-07-31
AU2018204015A1 (en) 2018-06-21
EP3186227A1 (en) 2017-07-05
JP2017530093A (ja) 2017-10-12
WO2016033341A1 (en) 2016-03-03
EP3186227B1 (en) 2021-03-24
KR20170036043A (ko) 2017-03-31
AU2015308828B2 (en) 2018-03-29
CA2956512A1 (en) 2016-03-03
EP3792251B1 (en) 2024-02-14
EP2990403A1 (en) 2016-03-02
BR112017002750B8 (pt) 2023-10-24
KR101857401B1 (ko) 2018-05-11
BR112017002750A2 (pt) 2017-12-19
EP3792251A1 (en) 2021-03-17
DK3186227T3 (da) 2021-04-26
CA3083585A1 (en) 2016-03-03
NZ744117A (en) 2021-06-25
US10464889B2 (en) 2019-11-05
US10047040B2 (en) 2018-08-14
US20170226053A1 (en) 2017-08-10
ES2865121T3 (es) 2021-10-15

Similar Documents

Publication Publication Date Title
CN106660961A (zh) 作为抗蠕虫药的新的磺酰基氨基苯甲酰胺化合物
ES2632265T3 (es) Azinas sustituidas como plaguicidas
CN106470972B (zh) 新的磺酰基氨基苯甲酰胺化合物
CN101495462B (zh) 嘧啶衍生物及其作为杀虫剂的用途
TW200909421A (en) 1-(azolin-2-yl)amino-1,2-diphenylethane compounds for combating animal pests
KR101759458B1 (ko) 신규 화합물
WO2023073641A9 (en) Anthelmintic pyrrolopyridazine compounds
AU2013366506A1 (en) (Hetero) arylacrylamides for the control of ectoparasites
KR20200055973A (ko) 오가노설퍼기를 포함하는 피라졸 카복사마이드 화합물을 함유하는 살진드기제 조성물

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
CB02 Change of applicant information

Address after: Basel

Applicant after: Swiss Iran animal health care Co., Ltd.

Address before: Basel

Applicant before: Animal health company limited of Novartis of Switzerland

CB02 Change of applicant information
GR01 Patent grant
GR01 Patent grant